Two for the Upper East Side
by mySOLEloveisMASEY
Summary: Blair's complicated relationship with Chuck, loosely based on the Audrey Hepburn classic Two for the Road, C/B with the teensiest bit of N/B later on.
1. Prologue

**A/N **This is my second fanfic and my first multi-chapter story, reviews are greatly appreciated!! I do not own Gossip Girl, TCM, or Two for the Road

After being so unceremoniously rejected by Chuck and convinced by Serena to stay in New York, Blair Waldorf returned to her penthouse, crawled under her plush goose down covers, and wished that she could die.

Her whole life had collapsed around her and she felt more alone and unwanted than usual. The only time she had truly felt happy and desired was during her brief affair with Chuck. Even her clueless ex, Nate, had noticed how much happier she had become, and as soon as he wanted her back, she dumped Chuck and went back to Nate. Nothing had worked the way she had planned. After Chuck exposed their secret relationship, Nate wanted nothing to do with her, and she became a social leper. Her recent conversation with Chuck showed just how far she had fallen. Though she refused to admit it to herself, she felt something for Chuck and his rejection was the absolute worst. It was time for a new plan, but Blair had no idea as to what that new plan would be.

Realizing that her death wish wouldn't come true, Blair turned on TCM. It was Audrey Hepburn month so Blair was sure that she could watch a great movie and escape from her problems. She was shocked to see that _Two for the Road_ was on. It wasn't her favorite Audrey movie, but it was a good one. As the movie progressed, she found many parallels in the relationship between Joanna and Mark. One scene resonated the most in which Joanna has and affair and then comes back to Mark.

Joanna: "I'm Back"

Mark: "You humiliate me, you humiliated me and then you come back?"

Joanna: "That's Right"

Mark: "Thank God!"

That was how it was supposed to work. Chuck was supposed to take her back even after all the pain she had caused him. He had always been there for her, and Blair was going to make sure that he would take her back and that he would help her get back to where she belonged, the top of the UES food chain.


	2. Chapter 1

Blair left her penthouse and caught a cab to the Palace Hotel. She went to the 23rd floor and marched towards Chuck's suite. She banged on the door and was shocked when it opened. Chuck stood in front of her: disheveled, suprisingly sober, and covered in bruises.

"What do you want, Waldorf?"

Blair couldn't speak, she had never seen Chuck like this. He stared at her for a few minutes before moving to close the door. Blair saw her oppurtunity slipping away and decided to use some of Audrey's lines.

"I'm back."

"So what?" Chuck scoffed. His demeanor was icy, but his eyes showed how much she had hurt him.

"I guess that_ I_ have to be more succinct, earlier _you rejected me_ when I came groveling back. However, Waldorfs don't grovel. So I refuse your rejection because I am erasing that embarassing episode from my life. I will say it once more:_ I'm back_."

"Wow, Waldorf your acting skills have definitely improved. I almost believed you were beig sincere, but then I remembered that Nate abandoned you and I was your second choice. Chuck Bass is no one's second choice."

"Chuck," Blair hesitated, "... you know what, never mind" she turned and started to leave.

"Blair, wait" Chuck swiftly grabbed her arm and turned her to face him, "What did you want to say."

In a barely audible voice Blair replied "I chose you." Chuck seemed perplexed "When did you choose me?"

"I chose you to be my first. You asked me if I was sure and I was. I chose to date you and if you hadn't ruined my cotillion, we might still be dating."

"Actually, Waldorf, you came to me after Nate dumped you, and when I went to find you at the cotillion to apologize and explain what happened, you were making out with Nate."

"No wonder you're failing history Bass, your recall of events are a little off. I went to see you after _I_ dumped Nate. _I kissed You_. I went to Nate after _You_ ruined my debut!"

"You knew I was there didn't you?"

Blair was speechless, she could never figure out if she hooked up with Nate because she loved him, or because she wanted to piss off Chuck. Chuck easily picked up on her indecision and took this as an answer to his question, "Were you trying to make me.. jealous?"

"No!" Blair responded a little too quickly.

"I knew you couldn't resist me, Waldorf"

"I have been resisting you 'charm' for years, Bass"

"Then why are you here?"

"_I'm back_!"

They stood there in silence, while they processed the meaning of their words. Chuck took a step towards Blair and she turned to meet him. He sweetly kissed her forehead and led her downstairs. He called his limo and sent her home with a chaste kiss on the lips.


	3. Chapter 2

Blair left Constance Billiard with an uncharacteristic smile on her face. Ever since she and Chuck had started seeing eachother, she seemed to radiate happiness. It had only been three hours since she had last seen Chuck, for a brief make-out session in an empty classroom. but she was already wanting to see him again. She wasn't "missing" him, she just really wanted to see him because it felt like an eternity since she had been with him. Blair pulled out her En-V, and quickly dialed Chuck's number.

"Miss me already, Waldorf?"

"Don't flatter yourself, Bass! I did not miss_ you_ at all, but I was wondering if you were up for a repeat of lunch?"

"Depends, what will you be wearing?"

"Bass, you are _so_ disgusting."

"Yet, you keep coming back for more."

"Whatever, I'm coming over in two hours."

"Why the wait?"

"I have to get ready."

Even though Blair and Chuck weren't officially dating, she still felt the need to prepare herself, as though she were going on a date. Blair changed out of her Constance Billiard uniform and put on a black Nanette Lepore dress with Chanel ballet flats. She fixed her hair, put on a red headband, grabbed her Birkin bag, and went to the Palace. Chuck wanted to prove to Blair that he could be romantic. All day he had planned the best way to prove it. He ordered her favorite foods, scattered rose petals around his suite, and dimmed the lights. When Blair arrived, she was shocked, Chuck's suite was beautiful and she knew that he had done it just for her.

"Hey beautiful,"

"Chuck, no one's ever done something like this for me, Thank You!"

"Well, Waldorf, I know that you want the best, I mean why else would you be dating me?"

Blair gasped, he said the "d" word. Chuck doesn't date. Blair was unsure of what to say. Chuck sense her hesitation and wanted to take back what he had said. Blair saw his face fall, and quickly said, "You know me well." Chuck's face lit up, he couldn't understand why this made him so hapy. but it did. Chuck gave Blair a passionate kiss and led her over to the dinner table. They ate in comfortable silence, enjoying eachother's company. Chuck looked at Blair with such passion that she blushed.

"Waldorf, you look ravishing tonight."

"Well I know how much you like to ravish me."

Chuck had never seen Blair act this flirty, until that glorious night at Victrola. They had always had a playful banter, but it had become filled with innuendo. Blair was beginning to realize that she was always happy with Chuck, and comfortable in their conversations. Now seemed like the oppurtune for Chuck to show Blair how he felt.

"Waldorf, I know we've only been together for a short time, but this is the lingest relationship that I've had. This is for you."

Chuck pulled out a Tiffany-blue box and handed it to Blair. She opened it and was greeted by a diamond butterfly pendant on a white gold chain. Chuck delicately put it on her, and began to slowly kiss her neck, Blair turned around and pounced on him. They spent the night together, and woke up in eachother's arms.


	4. Chapter 3

Blair woke up to the feeling of Chuck's lips on her own."Good Morning!"cooed Blair.

"It is a good morning, but I have a few ideas on how we could make it better."

"As much fun as I'm sure that would be, we have school, and I have a reputation to uphold. I need to get to school early, and I should arrive alone."

"What? Are you seriously ashamed of being seen with me? Because, last night you seemed pretty satisfied."

"Chuck, it's too soon, what would Nate think?"

"Waldorf, why does it matter? You're _my _girlfriend, and I was under the impression that couples wanted to spend time with eachother."

"And we do. I'm just not ready to go public."

"Fine. Whatever. Do what you want." Chuck got up, grabbed his clothes, went into the bathroom, and slammed the door. Blair let out a frustrated sigh. Why couldn't he understand? She needed to portray a certain image, at least until she was popular again; and dating the womanizer of the UES was not the type of popularity she wanted. Some sacrifices would have to be made for her to regain her position. She would make Chuck understand later today. Blair left the Palace, and returned to her own penthouse to get ready.

When Blair arrived at school, she was surprised to see that Chuck was already there and talking to Hazel, the new queen (for the time being). Blair was furious. Just because they had gotten into a fight, did not mean the Chuck could go flirt with Blair's replacement. Blair marched up to Chuck, and demanded that he speak with her privately, pulling him by his scarf.

"Easy, Waldorf, I just got this."

"Well seeing as I was the one that gave it to you, I know that it's new. What the hell is your problem?"

"What's my problem? You grabbed me. Oh, I get it you needed to see me privately so that I could satisfy you. Sorry, I'm not in the mood right now."

"NO! I do not want you or your body, but I would like to know why my_ boyfriend_ was talking to my arch-enemy."

"Believe it or not, I was trying to help you."

"Really, and how does seducing Hazel help me?"

"Well, first of all: I have my own reputation to uphold, no one knows that we are dating. Secondly, she gave me quite a lot of information on Jenny, including some photos that she is using to ensure that Jenny doesn't steal her crown. But since you don't believe me or want to associate with me in public, take this, I'll see you later." Chuck handed Blair Hazel's phone and walked into St. Jude's. Hazel's phones contained pictures of Jenny picking her nose, and a wedgie, and pole dancing in her underwear. Blair sent these photos to Gossip Girl via Hazel's phone. Jenny Hazel were spotted arguing a few minutes later, and Jenny was an outcast by lunch. Blair should have been euphoric, but instead she was upset over her accusations towards Chuck. She needed to do something to prove that she really did want to be with him. Blair took a deep breath and realized what she had to do. She sent Gossip Girl a message detailing her relationship with Chuck, including pictures. Less than five minutes later, everyone was staring at Blair. Chuck found Blair through the crowd, his eyes showed his confusion. Blair just smiled, and kissed him in front of everyone to the sound of camera-phones flashing pictures.


	5. Chapter 4

**A/N Sorry that it has taken me so long to post this, school has been crazy lately, I am already partially through the next chapter and I will hopefully put it up soon! This chapter is more about Chuck trying to gain back his friendship with Nate. But the next chapter is all about CHAIR!!**

Ever since they had started dating, Chuck lived to make Blair happy. He wanted to make up for the hurtful things he had said. Blair had always seemed to get the short end of the stick: most people preferred Serena, Eleanor treated Blair with contempt, Harold moved to France, and Nate ... he had screwed her over more times than Chuck could count. Nate was also the only person that Chuck could place blame on. Serena didn't try to get people to like her more, Eleanor treated most people with contempt, and Harold was trying to be happy. Nate was the one that had crushed Blair, but as much as he wanted to make Nate suffer, Chuck knew that it wouldn't matter. Nate was still Chuck's best friend, and he needed to talk to him about solving a little problem.

Chuck's limo pulled up to the Archibald residence, and was flabbergasted when he walked into Nate's house and caught sight of Nate and Vanessa making out furiously on the couch. Chuck cleared his throat loudly, knowing that he was on thin ice with Nate and one rude comment would leave Chuck drowning. When he looked up, Nate was surprised to see Chuck, and couldn't help but realize that he missed him. Chuck took Nate's silence as an opportunity to talk.

"Nathaniel, I hope I'm not interrupting anything too serious, but you and I need to talk."

"Chuck, now is not the best time for this, and I'm pretty sure that I told you to stay the hell away from me."

"And while I understand that, I have a proposition for you."

"Why would any proposition that you have, make me change my mind?"

"It would help your family," Chuck knew that Nate valued his family above everything else, and since Nate's family was falling apart, he would do anything to help bring it back together. Nate suddenly realized that he was still on top of Vanessa, and he knew that she should leave before he would discuss the proposition with Chuck. Nate got up and Vanessa did the same. He walked her to the door and kissed her good-bye. After Vanessa left, Nate turned towards Chuck and said,"How on earth could _you_ possibly help _my_ family?"

"Well, Nathaniel, since your dad's stunt in rehab, he had trouble finding clients that want him as their legal representation. If you help me, I will ensure that your dad is put in charge of legal affairs at Victrola. Not only will this give your dad a job, it will also help to rebuild his credibility."

"Alright Chuck, what do you need me to do?"

"I need you to see if Jeremy slept with Penny, and if he did, I need you to get his tape of it."

"Chuck, stealing someone's sex tape, that's low even for you."

"Trust me, I have no interest in what Jeremy did with Penny. I just need proof that she slept with him."

"Why?"

"Not that you would really care, _Nate_, but Penny helped to ruin Blair's life and I'm going to fix it. Penny will be ruined, and Blair will be popular again. Consequently, I am sorry for everything that happened, I never meant for this to work out the way it did."

"I'll find out what I can, but this doesn't mean that we're friends again!"

"Of course not," Chuck smirked. His plan was working perfectly, he would help restore Blair's reputation, destroy Penny, and get his friendship with Nate back. Chuck decided that there was no reason for him to stay at Nate's house, so he called his limo and left the Archibald residence. Chuck decided to pay Blair a visit. When he got there, he could hear Serena talking.

"Blair, I love that you're happy, but can't you be happy with someone else. Chuck is horrible and you could do so much better."

"Serena, I could say the same about you and Brooklyn. And besides, you will probably never understand but Chuck loves me and I love him. I don't want anyone else. Even if Nate decided to forgive me, I would still stay with Chuck."

Chuck, basking in the glory of what was just said, decided to make his presence known, "Good afternoon, Queen B, and _my dear sister_." Serena held her tongue, and decided to leave the couple alone before they got frisky. Chuck had a genuine smile on his face, and Blair grew worried.

"Why are you so happy?"

"Well, I have the best girlfriend, a plan to ruin Penny, and Nate and I will be friends soon."

Blair was curious as to what Chuck was planning, but she realized that Chuck wasn't going to tell her without some "persuasion."


	6. Chapter 5

A/N thank so much to everyone that reviewed, it really does encourage me to write more.

After successfully "persuading" Chuck, but failing to gain any information... twice, Blair gave up and went shopping with Serena. Chuck lay in Blair's bed going over his plan to help Blair reclaim her throne. He knew that he needed to tell Blair his plan, especially after not telling Blair what he had planned for Cotillion, blew up in his face, he just didn't know how to tell her. He didn't want to build her hopes up, and he needed to make sure that no one implicated Blair. But, the worst part was the fact that Penny wouldn't go down without trying to destroy Blair first. Chuck's thoughts were interrupted by a text from Nate.

**"Jeremy and Penny did it, meet me at his house tomorrow"**

As much as Chuck hated that Blair and would be publicly humiliated once again, it was the only way that could be crushed. But, if Chuck could explain it to her, and sweeten her up just a little bit, everything should be okay. Tonight would have to be perfect for, to help Blair prepare for what was to come. Chuck texted Blair to meet him at the Palace Hotel, at 7 O'clock for a night she wouldn't forget. At 6:45, Blair was in the lobby. She was about to go upstairs when she felt a pair of hands wrap around her waist. She turned around and kissed Chuck.

"Wow, Waldorf, do you always kiss strangers that walk up behind you?"

Blair rolled her eyes, "No, just ones that smell like you."

"You kissed my dad!? But seriously, are you ready for dinner?"

"Of course, especially because you promised that it would be memorable."

"Oh, it will be memorable."

"What's that supposed to mean?"

"Nothing, let's go eat."

Chuck took Blair to Socialista for dinner. He had reserved a quiet table in the back so that he could have Blair's full attention, but he took her to Socialista because he knew she wouldn't cause a scene in a restaurant. After they had ordered their food, Chuck decided he should just tell Blair the truth.

"Blair, I have something to tell you and you're not going to like it. I'm trying to help you get your crown back, so I need to destroy Penny. I've tried to blackmail her, but she didn't buy it. However, I can't release her sex tape, that I'm getting tomorrow, for no reason because I could be expelled or possibly arrested. Either way, Bart would not be pleased. Therefore, she needs to do something that would ensure that I couldn't be caught, because she would be caught for doing something wrong as well. In order for this to happen, she would have to do something mean to you."

"Seriously, Chuck, you want me to be publicly humiliated yet again."

"No, Blair, I don't want to humiliate you, but believe me, I've exhausted every other option. Blair, please listen to me, I'm trying to help you get your power back."

"And why should I believe you? How do I know that this isn't some sick joke for your own amusement."

"Because, Blair, I ... uh...I..l-lo-love you!"

Blair was speechless, at first she thought that he was just saying it to distract her. However, when she looked into his eyes, she saw that he was being honest and sincere.

"Just because you say that you love me, does not mean that I'm not mad."

"I know, believe me, I didn't mean to say that. I understand that you are upset, you have every reason to be mad at me. Just, promise me that you'll stay for the rest of the date. If you still hate me by the end of the date, I won't go through with the plan."

"Alright, but it would take a lot to make me want to go through with this ridiculous plan of yours."

After they finished eating, Chuck paid the check, and escorted Blair into the limo. She refused to sit near him. Blair began to get confused when she saw that they were leaving the Upper East Side. Her confusion grew, when they reached a nondescript building and the limo stopped. Blair had no idea as to where they were or why they were there. Chuck opened the door and helped Blair out of the limo.

"Bass, where are we?"

"Waldorf, I am shocked that you don't recognize where we are. You've _seen_ this place a hundred times, you've just never _been_ here."

"Wait, is this Holly Golightly's apartment?"

"Well, why don't we go inside and find out."

Chuck and Blair climbed the 13 flights of stairs to her apartment. Chuck had rented the apartment and decorated it with pictures of Blair and all of her friends. The whole apartment looked exactly as it did in the movie. Blair squealed with delight. Inside the apartment, a huge party was taking place. Everyone was packed into the living room. Chuck had invited all of Blair's friends and they had all been instructed to wear vintage designer clothes. Blair could not believe that Chuck had created this whole party, just to appease her. Consequently, Blair's anger began to subside. She realized that Chuck was just trying to help her, the only way he knew how. Blair kissed Chuck on the cheek, and danced the night away. At 5:45, Blair had finally become exhausted and left the apartment with Chuck. When they got in the limo, Blair was greeted with the smell of warm croissants. Blair was starving, she went to grab the croissants, but Chuck stopped her.

"Hands off, Waldorf, this date is not over yet. You will get to eat them soon enough."

"What else could we possibly do, it's morning."

Right then, the limo stopped in front of Tiffany's. Blair gasped as she realized that he was recreating the classic opening scene of her favorite movie. They got of the limo, and ate their croissants while the sun started to rise. Just when Blair thought it couldn't get any better, a string quartet began to play Moon River. She was touched by how much Chuck loved her. She turned to him and couldn't help but smile.

"I love you, Chuck Bass. You are the most amazing guy that I have ever known."

Blair leaned in towards Chuck, and kissed him with the passion of a heart filled with love. It had been the best date of her life!


	7. Chapter 6

**A/N: Sorry I haven't updated in a while, I have had AP Exams and almost done with Senior Year. I'm not sure what I think of this chapter, but I tried.**

Blair woke up next to Chuck, with a smile on her face. Everything seemed to be falling into place. She had a boyfriend that loved her, great grades, and was close to regaining her popularity. Think of this, Blair sighed. She was not looking forward to being humiliated again. Her dethroning had made her realize that she didn't have to be popular to be in control. Her true friends were the people that still associated with her after her fall from power. They accepted her for who she was, they didn't mind that she was a bitch, because that was part of the Blair that they knew and loved. Not that she didn't want to be popular, she loved the power and control. It was just that she now knew that her world wouldn't end if she wasn't at the center of it. Blair was pulled out of her reverie when she felt a heavy weight upon her. Blair attempted to move Chuck off of her, but he was too heavy. She then tried yelling in his ear, but he didn't budge. Blair was frustrated and Chuck was crushing her, so she decided to knee him in the groin. Chuck was woken up by a sharp pain in his crotch, he looked down and saw that he was on top of Blair.

"What the hell was that for?"

"Well I tried every other way to wake you up, but you remained unresponsive."

"Thanks for curbing my sex life for the next week."

"What do you mean?! It's not that bad."

"True, but why would I want to sleep with the girl that temporarily damaged my goods."

"That is so not fair! It's not my fault that you can sleep through a tornado."

"Well maybe I wouldn't have been so tired, if _somebody_ hadn't decided that we _had _to watch Breakfast at Tiffany's to end our date at 7:30 in the morning."

"You are such a drama queen."

"Wait, what time is it?"

"2:30, why?"

"I need to go to Jeremy's house, there's something I need to get."

"Bye, Paul. I Love You!"

"Love You too, Holly!" Chuck said as he quickly got dressed and made his way to Jeremy's house.

Jeremy lived close to Nate, and Chuck arrived 15 minutes after leaving Blair. When he got there, Chuck was surprised to find Nate sitting on the couch, talking to Jeremy. Chuck cleared his throat and the two boys turned to see who entered.

"Jeremy, Nathaniel."

"Chuck," they replied in unison.

"Well as much fun as you guys were having, I was wondering if we could sit down and talk."

"Right, but before we do that, Jeremy do you still have Kati's phone number?" Nate asked.

"Yeah, sure, let me go get it."

As soon as Jeremy left the room, Nate pulled a flash drive out of his pocket.

"Here's the video, now make some excuse to leave when Jeremy gets back, because I really don't want to be around you."

"Thanks, Nathaniel, this means a lot."

"I didn't do it for you, I did it for my family."

"Yes, I have already spoken to Bart and your father shall be named the chief officer of legal affairs concerning Victrola. Give my regards to Jeremy."

Chuck left Jeremy's house and returned to his suite to make a few last minute arrangements before Monday. Hazel would finally get what she deserved and Blair would be one step closer to getting her crown. Chuck's signature smirk alerted everyone to the fact that he was going to destroy someone. Blair, on the other hand, was nervous. The endless game of tug-of-war had risen to new heights. She knew that tomorrow would be the culmination of the social war, and Blair would be humiliated once again. However, this time it would be worth it because Hazel would be deemed the loser. Chuck was going to ensure that Blair won and he would do anything to achieve his goal. At the thought of Chuck, Blair couldn't help but smile. Chuck Bass had proven that he was the guy for her. She now knew that Nate was the first guy she fell for, but Chuck was her first love. The best part was that Chuck truly loved her, he cared deeply for her and would do anything if it would make her happy. She needed to play her part in his plan so that he could have the satisfaction of pleasing her.

-Scene Change: The next day (Monday)-

Blair awoke with a feeling of uncertainty, she had no idea how the day would go. She really wanted to trust Chuck, but his plan wasn't exactly fool-proof. She looked over at Chuck, snoring loudly with his arms wrapped around her. He was trying so hard to be the perfect boyfriend, he was the only person she would ever surrender partial control to. However, if she didn't hurry, she would ruin her perfect attendance record. She kissed Chuck to wake him up and went searching for her discarded clothes. After 20 minutes of actively scouring Chuck's suite, she had found everything but her trademark tights. Blair decided to forget about her tights and just leave for school with Chuck. They arrived 10 minutes before school would start. Chuck squeezed Blair's hand, and she smiled back reassuredly. Hazel appeared out of nowhere and enveloped Blair in a hug. Blair was so confused by Hazel's burst of affection that she failed to notice the _snip snip_ sound that pervaded the air. Suddenly, Blair felt a breeze and heard everyone laughing. She looked down to be greeted by her Agent Provacateur black lace thong on the ground.

"God, Blair, I knew that you were easy, but I didn't realize just how easy you were," Hazel cackled.

Blair turned bright red from embarassment. However, less than 30 seconds later, everyone received a copy of Hazel and Jeremy's sex tape. Blair was no longer the subject of laughter, she turned to Hazel and smiled.

"I always thought you were easy, but I didn't know that you were stupid too. Who else is dumb enough to tape their sex life?"

Blair walked off with Chuck too a small secluded area.

"Truth be told, Waldorf, I prefer you without underwear."

"Your heinous, Bass."

"I am, so why be shy? I know better than anyone that you are no longer as untouched as fresh snow."

"Why do you insist on comparing my non-virginal status to other things?"

"I enjoy getting a rise out of you. So, now that you have accomplished total social destruction, how about we go back to my suite and celebrate."

"Nothing would make me happier."

They left the courtyard between St. Jude's and Constance Billiard and returned to suite 1812 to celebrate their victory.


End file.
